CH637102A5 - Procede de preparation de chlorure de chloracetyle. - Google Patents
Procede de preparation de chlorure de chloracetyle. Download PDFInfo
- Publication number
- CH637102A5 CH637102A5 CH234279A CH234279A CH637102A5 CH 637102 A5 CH637102 A5 CH 637102A5 CH 234279 A CH234279 A CH 234279A CH 234279 A CH234279 A CH 234279A CH 637102 A5 CH637102 A5 CH 637102A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chloride
- glycolic acid
- catalyst
- mol
- reaction
- Prior art date
Links
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 13
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 48
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 15
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- -1 N, N-disubstituted amide Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 235000013877 carbamide Nutrition 0.000 claims description 4
- 150000003672 ureas Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 claims description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical group CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GNGUMAGSNTVFLB-UHFFFAOYSA-N 3-butyloxolan-2-one Chemical compound CCCCC1CCOC1=O GNGUMAGSNTVFLB-UHFFFAOYSA-N 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- GSSHGHPBCWUHPB-UHFFFAOYSA-N 4-chloro-2-hydroxy-3-oxobutanoyl chloride Chemical compound ClC(=O)C(O)C(=O)CCl GSSHGHPBCWUHPB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/891,429 US4129595A (en) | 1978-03-29 | 1978-03-29 | Preparation of chloroacetyl chloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH637102A5 true CH637102A5 (fr) | 1983-07-15 |
Family
ID=25398166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH234279A CH637102A5 (fr) | 1978-03-29 | 1979-03-12 | Procede de preparation de chlorure de chloracetyle. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4129595A (enrdf_load_stackoverflow) |
| JP (1) | JPS54151911A (enrdf_load_stackoverflow) |
| CA (1) | CA1116630A (enrdf_load_stackoverflow) |
| CH (1) | CH637102A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2909444A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2421164A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2017696B (enrdf_load_stackoverflow) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2943432A1 (de) * | 1979-10-26 | 1981-05-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von carbonsaeurehalogeniden |
| DE3019526A1 (de) * | 1980-05-22 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von chlorameisensaeurearylestern |
| JPS6030666B2 (ja) * | 1980-08-20 | 1985-07-17 | 鐘淵化学工業株式会社 | 光学活性メルカプトカルボン酸の製造法 |
| DE4116365A1 (de) * | 1991-05-18 | 1992-11-19 | Basf Ag | Verfahren zur herstellung von alkyl-, alkenyl- und alkinylchloriden |
| AU727200B2 (en) | 1996-03-15 | 2000-12-07 | Dow Agrosciences Llc | Halogenation catalyst |
| DE19753773A1 (de) * | 1997-12-04 | 1999-06-10 | Basf Ag | Verfahren zur Herstellung von Chlorcarbonsäurechloriden |
| US7435849B2 (en) | 2005-10-31 | 2008-10-14 | Hoffmann-La Roche Inc. | Process for the production of acid chlorides |
| ES2395167T3 (es) * | 2007-04-25 | 2013-02-08 | F. Hoffmann-La Roche Ag | Nuevo proceso para la obtención de cloruros de ácido |
| KR101279751B1 (ko) * | 2008-04-04 | 2013-07-04 | 에프. 호프만-라 로슈 아게 | 사이클로헥산카복실산 유도체의 제조 방법 |
| AU2009231424B2 (en) * | 2008-04-04 | 2014-01-30 | F. Hoffmann-La Roche Ag | New process for the preparation of cyclohexanecarboxylic acid derivatives via the corresponding cyclohexanecarboxamide derivative |
| KR101644222B1 (ko) | 2008-06-17 | 2016-07-29 | 에프. 호프만-라 로슈 아게 | 약학 활성 아미드의 제조에서 중간체로서의 1-(2-에틸-부틸)-사이클로헥산카복실산 에스터 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899458A (en) * | 1959-08-11 | Process for producing oxy aromatic | ||
| US2889365A (en) * | 1957-06-27 | 1959-06-02 | Monsanto Chemicals | Process for producing monochloroacetyl chloride by chlorinating ketene in sulfur dioxide |
-
1978
- 1978-03-29 US US05/891,429 patent/US4129595A/en not_active Expired - Lifetime
-
1979
- 1979-02-12 CA CA000321297A patent/CA1116630A/en not_active Expired
- 1979-03-10 DE DE19792909444 patent/DE2909444A1/de active Granted
- 1979-03-12 CH CH234279A patent/CH637102A5/fr not_active IP Right Cessation
- 1979-03-22 FR FR7907258A patent/FR2421164A1/fr active Granted
- 1979-03-27 GB GB7910703A patent/GB2017696B/en not_active Expired
- 1979-03-28 JP JP3681779A patent/JPS54151911A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4129595A (en) | 1978-12-12 |
| JPS54151911A (en) | 1979-11-29 |
| FR2421164B1 (enrdf_load_stackoverflow) | 1983-01-07 |
| DE2909444A1 (de) | 1979-10-11 |
| FR2421164A1 (fr) | 1979-10-26 |
| GB2017696A (en) | 1979-10-10 |
| CA1116630A (en) | 1982-01-19 |
| GB2017696B (en) | 1982-11-10 |
| JPS5726657B2 (enrdf_load_stackoverflow) | 1982-06-05 |
| DE2909444C2 (enrdf_load_stackoverflow) | 1989-02-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH637102A5 (fr) | Procede de preparation de chlorure de chloracetyle. | |
| FR2556347A1 (fr) | Nouveau compose organophosphore cyclique et son procede de fabrication | |
| JPS6366308B2 (enrdf_load_stackoverflow) | ||
| US6127583A (en) | Process for preparing acetylene derivative from a ketone compound | |
| JPH01268663A (ja) | モノグリセリドの製造方法 | |
| US3867437A (en) | N-acyl-N{40 -substituted-2,6-diamino-benzoic acids and process for making the same | |
| EP0435714B1 (fr) | Procédé de préparation de chlorures d'acides carboxyliques chlorés | |
| CA2243667A1 (fr) | Synthese d'acides carboxyalkylthiosucciniques | |
| JP3338101B2 (ja) | アリールアクリル酸類及びそれらのエステル類の製造方法 | |
| US20060258886A1 (en) | Alpha, omega-difuctional aldaramides | |
| SU422138A3 (enrdf_load_stackoverflow) | ||
| JPH0717935A (ja) | ３−アミノプロピオニトリルの製造法 | |
| EP0001847B1 (en) | Process for the preparation of alkenyl cyanoacetates | |
| JP7628947B2 (ja) | マラチオンの触媒による環境に優しい製造方法 | |
| JPH0142253B2 (enrdf_load_stackoverflow) | ||
| Gupton et al. | Two Convenient Syntheses of 2-Aryl-1-Cyano-1-Propenes From Quaternary Ammonium Salts | |
| US4246200A (en) | Perfluoro intermediates and processes for their preparation | |
| US4105687A (en) | Cyanoethylation of glycolic esters | |
| EP0036441B1 (de) | Verfahren zur Herstellung von Carbonsäurecyaniden | |
| JPH01242537A (ja) | ２−フルオロビフェニル誘導体の製造方法 | |
| JPS63188650A (ja) | メタクリル酸エステルの製造方法 | |
| RU2019542C1 (ru) | Способ получения бензамида | |
| JPH06122654A (ja) | 高光学純度のβ，β，β−トリフルオロ乳酸エステル化合物の製造方法 | |
| JPS617261A (ja) | ３−置換−２−オキサゾリジノン化合物の製造法 | |
| JPH0365340B2 (enrdf_load_stackoverflow) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |